EP2226371B1 - Composition adhésive, et plaque polarisante adhésive et dispositif d'affichage à cristaux liquides la comprenant - Google Patents

Composition adhésive, et plaque polarisante adhésive et dispositif d'affichage à cristaux liquides la comprenant Download PDF

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Publication number
EP2226371B1
EP2226371B1 EP09700483.2A EP09700483A EP2226371B1 EP 2226371 B1 EP2226371 B1 EP 2226371B1 EP 09700483 A EP09700483 A EP 09700483A EP 2226371 B1 EP2226371 B1 EP 2226371B1
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Prior art keywords
sensitive adhesive
pressure
adhesive composition
weight
acrylate
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German (de)
English (en)
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EP2226371A4 (fr
EP2226371A2 (fr
Inventor
Jeong Min Ha
No Ma Kim
In Ho Hwang
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LG Chem Ltd
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LG Chem Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B32B2457/202—LCD, i.e. liquid crystal displays
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/03—Viewing layer characterised by chemical composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/03—Viewing layer characterised by chemical composition
    • C09K2323/031—Polarizer or dye
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/03—Viewing layer characterised by chemical composition
    • C09K2323/035—Ester polymer, e.g. polycarbonate, polyacrylate or polyester
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/05—Bonding or intermediate layer characterised by chemical composition, e.g. sealant or spacer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/05—Bonding or intermediate layer characterised by chemical composition, e.g. sealant or spacer
    • C09K2323/057—Ester polymer, e.g. polycarbonate, polyacrylate or polyester
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
    • C09K2323/05—Bonding or intermediate layer characterised by chemical composition, e.g. sealant or spacer
    • C09K2323/059—Unsaturated aliphatic polymer, e.g. vinyl
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133528—Polarisers
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2202/00—Materials and properties
    • G02F2202/28—Adhesive materials or arrangements
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/141—Feedstock

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition having excellent physical properties under high temperature and/or high humidity conditions, and light leakage-preventing property; a polarizer; and a liquid crystal display comprising the same.
  • the liquid crystal display is a device representing images by liquid crystals inserted between two sheets of thin glass substrates.
  • the molecular alignment manner of liquid crystals changes, whereby transmission ratio of lights passing through the liquid crystals is changed, so that pictures or colors may be represented.
  • Such a liquid crystal display has advantages that it uses very little power and can be flatly and thinly made. Therefore, it is a display device being in the limelight of various fields at present.
  • liquid crystal cells comprising liquid crystals and glass substrates having transparent electrode, and polarizers are basically required and suitable adhesives or pressure-sensitive adhesives are also required for binding them.
  • the polarizer comprises an iodine compound or a dichroic polarizing material aligned in a certain direction, and has multi-layer structure comprising TAC (triacetyl cellulose) protective films for protecting polarizing elements, and the like.
  • the polarizer may additionally comprise a phase difference film, a compensation film for wide view angle or a brightness enhancement film, and the like.
  • Each film constituting these multi-layer polarizers is made of materials having different molecular structures and compositions, and so has different physical properties. Thus, under high temperature and/or high humidity conditions, it has inferior dimensional stability, since shrinkage or expansion behavior of the materials having a unidirectional molecular alignment is different. Therefore, if the polarizer is fixed by a pressure-sensitive adhesive, stress is concentrated on the TAC layer by shrinkage or expansion under high temperature and/or high humidity conditions, thereby birefringence and light leakage phenomenon occur.
  • the pressure-sensitive adhesive composition disclosed in said techniques has very poor tailoring property.
  • crooking or pressing phenomenon is arisen in the pressure-sensitive adhesive. So, there is a problem that yield is highly lowered.
  • the pressure-sensitive adhesive As other technique for preventing light leakage phenomenon, there is a method for designing the pressure-sensitive adhesive to be very hard.
  • the pressure-sensitive adhesive has hard property, shrinking or expansion of the polarizer under high temperature and/or high humidity conditions is suppressed, whereby the resulting stress is minimized and focused on the outermost, so that relatively good optical properties may be realized.
  • all pressure-sensitive adhesive compositions disclosed in said publications all employ an activating energy ray-curing system. That is, all pressure-sensitive adhesive compositions of the publication comprise photoinitiator as essential component, and the photoinitiator transforms a multi-functional acrylate into polymer, so as to form a secondary crosslinking structure by UV irradiation.
  • the present invention is accomplished considering the problems of the prior arts as described above, and is intended to provide a pressure-sensitive adhesive composition having excellent physical properties such as endurance reliability under high temperature and/or high humidity conditions and re-movability, and representing superior light leakage-preventing property even in case of being used in large display devices with a size of 20 inches or more, a polarizer and a liquid crystal display using the same.
  • the present invention provides a pressure-sensitive adhesive composition, including interpenetrating polymer networks in a cured state, wherein the composition comprises a multi-functional acrylate and a thermal initiator according to claim 1.
  • the present invention provides a polarizer comprising a polarizing film or a polarizing device; and a pressure-sensitive adhesive layer which is formed on one or both sides of said polarizing film or device, and comprises a cured product of the pressure-sensitive adhesive composition according to the present invention.
  • the present invention provides a liquid crystal display comprising a liquid crystal panel in which the polarizer according to the present invention is bonded to one or both sides of a liquid crystal cell.
  • the pressure-sensitive adhesive composition which has excellent physical properties such as endurance reliability under high temperature and/or high humidity conditions and re-movability, and representing superior light leakage-preventing property even in case of being used in large display devices with a size of 20 inches or more, a polarizer and a liquid crystal display using the same.
  • Fig. 1 is a graph showing change ratio of luminance observed at the horizontal axis of the monitor after applying the pressure-sensitive adhesive of Example 1 and Comparative Example 1 to 26 inch monitor.
  • the present invention relates to a pressure-sensitive adhesive composition, including interpenetrating polymer networks (hereinafter, it can be referred to as "IPN”) in a cured state, wherein the composition comprises a multi-functional acrylate and a a thermal initiator according to claim 1.
  • IPN interpenetrating polymer networks
  • the present invention also relates to a polarizer comprising:
  • the present invention also relates to a liquid crystal display comprising a liquid crystal panel in which the polarizer according to the present invention is bonded to one or both sides of a liquid crystal cell.
  • the present pressure-sensitive adhesive composition is described in more detail below.
  • the pressure-sensitive adhesive composition of the present invention includes IPN in a cured state
  • the term "cured state” used herein refers to a state in which the pressure-sensitive adhesive composition turns into a pressure-sensitive adhesive through a heating process, and the like.
  • the term “interpenetrating polymer networks” used herein refers to a state in which the pressure-sensitive adhesive comprises a crosslinking structure (hereinafter, it can be referred to as a "secondary crosslinking structure”) formed form reactions of the multi-functional acrylate and the thermal initiator together with a crosslinking structure (hereinafter, it can be referred to as a "primary crosslinking structure”) formed from a base resin.
  • composition of the present invention comprises an acrylic copolymer as the base resin forming the primary crosslinking structure.
  • the acrylic copolymer has a weight average molecular weight (M w ) of 1,000,000 or more. If the weight average molecular weight of said copolymer is less than 1,000,000, it is apprehended that the endurance reliability of the composition is lowered, so that bubbles or peeling phenomenon may be occurred due to lowered cohesion under high temperature and/or high humidity conditions.
  • the upper limit is not particularly restricted, but it is preferred that the upper limit is 2,500,000. If the weight-average molecular weight is in excess of 2,500,000, it is apprehended that the coating property is lowered due to increasing of viscosity, or endurance reliability is deteriorated due to lowering of pressure-sensitive adhesive force.
  • the specific composition of the copolymer used in the present invention is not particularly restricted, as long as it has the weight average molecular weight as described above.
  • the copolymer may be used herein, which comprises (meth)acrylic acid ester monomer and a monomer containing a cross-linkable functional group.
  • any kind of (meth)acrylic acid ester monomer may be used.
  • alkyl (meth)acrylate may be used.
  • Tg glass transition temperature
  • (meth)acrylic acid ester monomer having an alkyl group with 2 to 14 carbon atoms it is preferred to use.
  • An example of such a monomer may include one or more selected from the group consisting of ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate, sec-butyl (meth)acrylate, pentyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-ethylbutyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, lauryl (meth)acrylate and tetradecyl (meth)acrylate.
  • the (meth)acrylic acid ester monomer is comprised in an amount of 50 to 94 parts by weight, and preferably 70 to 94 parts by weight, based on 100 parts by weight of the copolymer. If said content is less than 50 parts by weight, it is apprehended that the initial adhesion strength of pressure-sensitive adhesive is lowered. If it is in excess of 94 parts by weight, it is apprehended that a problem is caused in durability due to lowered cohesion.
  • the monomer containing a cross-linkable functional group gives a cross-linkable functional group to the acrylic copolymer, and serves to control endurance reliability, adhesion strength and cohesion.
  • An example of usable monomers containing a cross-linkable functional group herein may include, but is not limited to, monomers containing a hydroxyl group, monomers containing carboxyl group, or monomers containing nitrogen. In the present invention, one or two or more of the foregoing monomers may be used.
  • An example of usable monomers containing a hydroxyl group herein may include, but is not limited to, one or two or more species of 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 2-hydroxyethyleneglycol (meth)acrylate or 2-hydroxypropyleneglycol (meth)acrylate.
  • An example of usable monomers containing a carboxyl group herein may include, but is not limited to, one or two or more species of (meth)acrylic acid, 2-(meth)acryloyloxy acetic acid, 3-(meth)acryloyloxy propylic acid, 4-(meth)acryloyloxy butylic acid, acrylic acid dimer, itaconic acid, maleic acid and maleic anhydride.
  • An example of usable monomers containing nitrogen herein may include, but is not limited to, one or two or more species of (meth)acrylamide, N-vinyl pyrolidone and N-vinyl caprolactam.
  • the monomer containing a cross-linkable functional group as above is contained in an amount of 0.01 to 10 parts by weight, and preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the copolymer. If said content is less than 0.01 parts by weight, it is apprehended the re-movability is deteriorated. If it is in excess of 10 parts by weight, it is apprehended that adhesiveness, durability and/or peel force is lowered.
  • the acrylic copolymer may further comprise a monomer containing an alkylene oxide group.
  • the monomer gives alkylene oxide to copolymer, and the alkylene oxide can reduce haze in a final product by increasing miscibility of the copolymer and the multi-function acrylate.
  • the alkylene oxide can make the pressure-sensitive adhesive have an excellent light leakage-preventing property by increasing bulk modulus when same amount of the multi-functional acrylate is used.
  • the alkylene oxide can improve durability, since it can make the adhesive to maintain good pressure-sensitive adhesive even in a state where the bulk modulus is much increased.
  • the alkylene oxide shows an excellent miscibility with the acrylate having at least 3 functional groups and comprising a cyclic structure in its skeleton.
  • An example of usable monomer containing an alkylene oxide group include, but is not limited thereto, (meth)acrylic acid alkylene oxide adduct.
  • An example of usable (meth)acrylic acid alkylene oxide adduct herein may include, but is not limited to, one or two or more species of alkoxy ethyleneglycol (meth)acrylic acid ester, alkoxy diethyleneglycol (meth)acrylic acid ester, alkoxy triethyleneglycol (meth)acrylic acid ester, alkoxy tetraethyleneglycol (meth)acrylic acid ester, phenoxy ethyleneglycol (meth)acrylic acid ester, phenoxy diethyleneglycol (meth)acrylic acid ester, phenoxy triethyleneglycol (meth)acrylic acid ester, phenoxy tetraethyleneglycol (meth)acrylic acid ester, alkoxy propyleneglycol (meth)acrylic acid ester, alkoxy diprop
  • the content of the (meth)acrylic acid alkylene oxide adduct is not specially limited, and it can be appropriately selected considering the above property.
  • the (meth)acrylic acid alkylene oxide adduct may be comprised in an amount of 2 to 40 parts by weight, based on 100 parts by weight of the acrylic copolymer.
  • a monomer represented in Formula 1 below may be further copolymerized. Such a monomer may be added for controlling glass transition temperature of a pressure-sensitive adhesive and giving other functions thereto.
  • R 1 , R 2 and R 3 represents independently hydrogen or alkyl
  • R 4 represents cyano; phenyl unsubstituted or substituted with alkyl; acetyloxy; or COR 5 , where R 5 represents amino unsubstituted or substituted with alkyl or alkoxyalkyl; or glycidyloxy.
  • alkyl or alkoxy means alkyl or alkoxy having 1 to 8 carbon atoms, and is, preferably, methyl, ethyl, methoxy, ethoxy, propoxy or butoxy.
  • the specific kind of monomer represented by the above Formula 1 may include, but is not limited to, one or two or more of nitrogen-containing monomers such as (meth)acrylonitrile, (meth)acrylamide, N-methyl (meth)acrylamide or N-butoxy methyl (meth)acrylamide; styrene monomer such as styrene or methyl styrene; glycidyl (meth)acrylate; or carbonic acid vinyl ester such as vinyl acetate, and the like.
  • the functional monomer as above is contained in the present acrylic copolymer, the content is, preferably, 20 parts by weight or less. If said content is in excess of 20 parts by weight, it is apprehended that flexibility and/or peel force of the pressure-sensitive adhesive is lowered.
  • the method for preparing the copolymer is not particularly restricted.
  • it can be prepared through general methods such as solution polymerization, photopolymerization, bulk polymerization, suspension polymerization, or emulsion polymerization.
  • solution polymerization is carried out at a polymerization temperature of 50 to 140°C by mixing an initiator in a state that each monomer is homogeneously mixed.
  • a usual initiator for example, an azo-based polymerization initiator such as azo-bisisobutyronitrile or azobiscyclohexanecarbonitrile; and/or a peroxide such as benzoyl peroxide or acetyl peroxide may be included.
  • an azo-based polymerization initiator such as azo-bisisobutyronitrile or azobiscyclohexanecarbonitrile
  • a peroxide such as benzoyl peroxide or acetyl peroxide
  • the present pressure-sensitive adhesive composition comprises a multi-functional acrylate together with the base resin as previously described.
  • the multi-functional acrylate serves to form the secondary crosslinking structure through a reaction with the thermal initiator.
  • an acrylate having a molecular weight of less than 1,000 and containing three or more functional groups is used.
  • an acrylate containing three or more functional groups physical properties such as endurance reliability and light leakage-preventing property may be further improved.
  • acrylate may include, but is not limited to, a trifunctional acrylate such as trimethylolpropane tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, propionic acid-modified dipentaerythritol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, propyleneoxide-modified trimethylolpropane tri(meth)acrylate, trifunctional urethane (meth)acrylate or tris(meth)acryloxy ethylisocyanurate; a tetrafunctional acrylate such as diglycerin tetra(meth)acrylate or pentaerythritol tetra(meth)acrylate; a pentafunctional acrylate such as propionic acid-modified dipentaerythritol penta(meth)acrylate; and a hexafunctional acrylate such as dipentaeryth
  • the cyclic structure may comprise carbocyclic or heterocyclic structure; or monocyclic or polycyclic structure.
  • An example of acrylate comprising the cyclic structure may include a monomer having isocyanurate structure such as tris(meth)acryloxy ethyl isocyanurate; and hexafunctional acrylate such as isocyanate-modified urethane (meth)acrylate (ex. a reactant of trimethylolpropane tri(meth)acrylate with an isocyanate monomer).
  • the multi-functional acrylate as above is, preferably, contained in an amount of 5 to 40 parts by weight, relative to 100 parts by weight of the base resin. If the content is less than 5 parts by weight, it is apprehended that light leakage-preventing property and/or durability under high temperature is deteriorated. If the content is in excess of 40 parts by weight, it is apprehended that durability under high temperature is deteriorated.
  • the present pressure-sensitive adhesive composition comprises a thermal initiator forming the secondary crosslinking structure by reacting with the multi-functional acrylate.
  • a thermal initiator having a 10 hours half-life decomposition temperature of 40°C to 80°C is used. If the temperature is less than 40°C, it is apprehended that it is difficult to use due to a excessive lowering of pot-life of a coating liquid. If the temperature is in excess of 80°C, shrinking problem of a base film is occurred, since high temperature is needed to accelerate heat-decomposition of the initiator during coating process.
  • thermal initiator which may be used herein is not particularly restricted, and may include, for example, one or more selected from the group consisting of azo compound such as 2,2-azobis-2,4-dimethylvaleronitrile (V-65, manufactured by Wako), 2,2-azobisisobutyronitrile (V-60, manufactured by Wako) or 2,2-azobis-2-methylbutyronitrile (V-59, manufactured by Wako); peroxy ester compounds such as dipropyl peroxydicarbonate (Peroyl NPP, manufactured by NOF), diisopropyl peroxy dicarbonate (Peroyl IPP, manufactured by NOF), bis-4-butylcyclohexyl peroxydicarbonate (Peroyl TCP, manufactured by NOF), diethoxy ethyl peroxy dicarbonate (Peroyl EEP, manufactured by NOF), diethoxyhexyl peroxy dicarbonate (Peroyl OPP, manufactured by NOF), hexyl peroxy
  • radical is generated.
  • hydrogen abstraction of the base resin ex. acrylic copolymer
  • addition chain reaction of the multi-functional acrylate are induced respectively or simultaneously.
  • the hydrogen abstraction is suppressed from the viewpoint of controlling pressure-sensitive adhesive property and durability. Therefore, it is preferable to use azo compound or acyl peroxide, and it is more preferable to use acyl peroxide.
  • the thermal initiator as above may be contained in an amount of 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, and more preferably 1 to 5 parts by weight, relative to 100 parts by weight of the base resin. If the content is less than 0.1 parts by weight, it is apprehended that efficiency to initiate reaction or reproducibility is deteriorated. If the content is in excess of 10 parts by weight, it is apprehended that durability is deteriorated due to remaining initiators.
  • the present pressure-sensitive adhesive composition further comprises a multi-functional cross-linking agent, which reacts with the base resin, and controls the pressure-sensitive adhesive property and cohesion.
  • cross-linking agent which may be used herein is not particularly restricted, and may include, for example, an isocyanate compound, an epoxy compound, an aziridine compound and a metal chelate compound.
  • isocyanate compound includes tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylxylene diisocyanate, naphthalene diisocyanate and a reaction product of any one of the foregoing with polyol (ex.
  • an example of the epoxy compound includes ethyleneglycol diglycidylether, triglycidylether, trimethylolpropane triglycidylether, N,N,N',N'-tetraglycidyl ethylenediamine and glycerin diglycidylether;
  • an example of the aziridine compound include N,N'-toluene-2,4-bis(1-aziridinecarboxamide), N,N'-diphenylmethane-4,4'-bis(1-aziridinecarboxamide), triethylene melamine, bisisophthaloyl-1-(2-methylaziridine) and tri-1-aziridinylphosphine oxide.
  • an example of the metal chelate compound includes compound in which multivalent metal such as aluminum, iron, zinc, tin, titan, antimony, magnesium and/or vanadium is being chelated to acetyl acetone or ethyl acetoacetate.
  • multivalent metal such as aluminum, iron, zinc, tin, titan, antimony, magnesium and/or vanadium
  • acetyl acetone or ethyl acetoacetate acetyl acetone or ethyl acetoacetate.
  • one or two or more of the forgoing may be used alone or in a mixture thereof.
  • the cross-linking agent may be contained in an amount of 0.1 to 3 parts by weight, relative to 100 parts by weight of the base resin. If said content is less than 0.1 parts by weight, it is apprehended that the cohesion of the pressure-sensitive adhesive is lowered, since the cross-linking reaction is not well performed. If it is in excess of 3 parts by weight, it is apprehended that the endurance reliability is lowered by causing interlayer peeling or loosing phenomenon, since the cross-linking reaction is excessively proceeded.
  • the present pressure-sensitive adhesive composition may also comprise a silane coupling agent in addition to the components as described above.
  • a coupling agent improves adhesion and bonding stability between the pressure-sensitive adhesive and a glass substrate, whereby heat resistance and humidity resistance can be further improved.
  • the coupling agent serves to improve attachment reliability.
  • An example of usable coupling agnet herein may include, but is not limited thereto, ⁇ -glycidoxypropyltrimethoxy silane, ⁇ -glycidoxypropylmethyldiethoxy silane, ⁇ -glycidoxypropyltriethoxy silane, 3-mercaptopropyl trimethoxy silane, vinyltrimethoxy silane, vinyl triethoxy silane, ⁇ -methacryloxypropyl trimethoxy silane, ⁇ -methacryloxypropyl triethoxy silane, ⁇ -aminopropyl trimethoxy silane, ⁇ -aminopropyl triethoxy silane, 3-isocyanatopropyl triethoxy silane or ⁇ -acetoacetate propyl trimethoxy silane.
  • silane coupling agent is contained in an amount of 0.01 to 5 parts by weight in the composition, relative to 100 parts by weight of the base resin. If said content is less than 0.01 parts by weight, it is apprehended that the effect of increasing adhesion strength is slight. If it is in excess of 5 parts by weight, it is apprehended that the endurance reliability is lowered, so that bubbles or peeling phenomenon may be caused.
  • the present pressure-sensitive adhesive composition may further comprise 1 to 100 parts by weight of a tackifier resin, relative to 100 parts by weight of the base resin.
  • a tackifier resin is not particularly restricted, and may use one or two or more mixtures of a (hydrogenated) hydrocarbon resin, a (hydrogenated) rosin resin, a (hydrogenated) rosin ester resin, a (hydrogenated) terpene resin, a (hydrogenated) terpene phenol resin, a polymerized rosin resin, or a polymerized rosin ester resin, and the like.
  • the content of said tackifier resin is less than 1 part by weight, it is apprehended that the effect caused by adding it is slight. If it is in excess of 100 parts by weight, it is apprehended that the effect of improving compatibility and/or cohesion is lowered.
  • the present pressure-sensitive adhesive composition may further comprise one or more additives selected from the group consisting of an epoxy resin, a hardener, a UV stabilizer, an antioxidant, a colorant, a reinforcing agent, a filling agent, a defoaming agent, a surfactant and a plasticizer in a range of not affecting the effect of the present invention.
  • one or more additives selected from the group consisting of an epoxy resin, a hardener, a UV stabilizer, an antioxidant, a colorant, a reinforcing agent, a filling agent, a defoaming agent, a surfactant and a plasticizer in a range of not affecting the effect of the present invention.
  • the present invention relates to a polarizer, comprising:
  • a polarizing film or polarizing device constituting said polarizer of the present invention is not particularly restricted.
  • a film obtained by containing a polarizing component such as iodine or dichroic dye into polyvinyl alcohol resin film, and elongating the resulting product may be used as said polarizing film.
  • Said polyvinyl alcohol resin may comprise polyvinyl alcohol, polyvinyl formal, polyvinyl acetal and hydrolysate of ethylene-vinyl acetate copolymer, and the like.
  • the thickness of said polarizing film is also not particularly restricted. It may be formed in a usual thickness.
  • the polarizer may be formed as a multilayer film, wherein protective films, such as a cellulose film, for example, triacetyl cellulose; a polyester film, for example a polycarbonate film or a polyethylene terephthalate; a polyether sulphone film; and/or a polyolefin film, for example, polyethylene film, polypropylene film, polyolefin film having cyclo or norbornene structure, or ethylene-propylene copolymer, are laminated on one or both sides of the polarizing film.
  • the thickness of these protective films is also not particularly restricted. It may be formed in a usual thickness.
  • the present polarizer may further comprise one or more functional layers selected from the group consisting of protective layer, reflecting layer, anti-glare layer, phase difference plate, compensation film for wide view angle, and brightness enhancing film.
  • functional layers selected from the group consisting of protective layer, reflecting layer, anti-glare layer, phase difference plate, compensation film for wide view angle, and brightness enhancing film.
  • specific kind of material, preparation method, thickness of the functional layers is not particularly limited, and conventional ones can be applied.
  • the method of forming the pressure-sensitive adhesive layer on the polarizing film or device as above is not particularly restricted, and may be used, for example, as a method of coating and hardening the pressure-sensitive adhesive composition on said polarizing film with Bar Coater and the like, or a method of coating and drying the pressure-sensitive adhesive on the surface of releasable substrate and then, transferring the pressure-sensitive adhesive layer to the surface of polarizing film.
  • the crosslinking agent is controlled for cross-linking reaction of functional groups to be not performed on forming pressure-sensitive adhesive layer. That is, said crosslinking agent forms a cross-linking structure in drying and aging steps after coating to improve cohesion, whereby it may improve physical properties of pressure-sensitive adhesive articles such as adhesive property and cuttability.
  • the composition on forming said pressure-sensitive adhesive layer, it is preferred to use the composition after sufficiently removing components causing bubbles such as volatile ingredients or reaction residues within the composition. If the cross-linking density or molecular weight is excessively low and thus elasticity modulus is lowered, it is apprehended that scatterers are formed inside by magnifying small bubbles present between the glass plate and the pressure-sensitive adhesive layer at high temperature conditions.
  • the method of hardening the pressure-sensitive adhesive composition of the present invention is not particularly limited. For example, it is carried out by applying heat enough to activate the thermal initiator contained in the composition.
  • the gel content as represented in General Formula 1 below is preferably 80% to 99% and more preferably 90% to 99%.
  • G ⁇ e ⁇ l content % B / A ⁇ 100 wherein A represents weight of the pressure-sensitive adhesive, and B represents dry weight of insoluble content after depositing the adhesive in ethyl acetate at ambient temperature for 48 hours.
  • said gel content is less than 80%, it is apprehended that the endurance reliability under high temperature and/or high humidity conditions is lowered. If it is in excess of 99%, it is apprehended that the stress relief property of pressure-sensitive adhesive is lowered.
  • the present invention relates to a liquid crystal display comprising a liquid crystal panel, in which the polarizer according to the present invention is bonded to one or both sides of a liquid crystal cell.
  • liquid crystal cell constituting the liquid crystal display of the present invention as above, is not particularly restricted, and includes all general liquid crystal cells such as TN (Twisted Neumatic), STN (Super Twisted Neumatic), IPS (In Plane Switching) or VA (Vertical Alignment).
  • TN Transmission Neumatic
  • STN Super Twisted Neumatic
  • IPS In Plane Switching
  • VA Very Alignment
  • Specific kind of other construction included in the liquid crystal display of the present invention and process for preparing the same is not particularly restricted, and general constructions in this field may be selected and used without limitation.
  • n-BA n-butyl acrylate
  • HOA hydroxyl ethylacrylate
  • AIBN azobisisobutyronitrile
  • the resulting product was diluted with ethyl acetate (EAc) to prepare an acrylic copolymer having a solid content of 15 % by weight, a weight average molecular weight of 1,600,000, and a molecular weight distribution of 4.9.
  • EAc ethyl acetate
  • the pressure-sensitive adhesive composition as prepared above was coated on a polyethyleneterephthalate (PET) (MRF-38, manufactured by Mitsubishi Corporation) film that has been sujected to release treatment, and has a thickness of 38 micon to have a thickness of 25 micorn after dryness, and said film was dried in an oven at 135°C for 5 minutes. Then, the dried pressure-sensitive adhesive layer was stored at Temperature and Humidity Room Chamber (23°C, 55% RH) for about one day, and laminated on the WV coating layer of the polarizer that a WV (Wide View) liquid crystal layer was coated on one side.
  • PET polyethyleneterephthalate
  • MRF-38 manufactured by Mitsubishi Corporation
  • Pressure-sensitive adhesive compositions were prepared by the same method as Example 1, except that components as shown in Table 1 below were mixed with the acrylic copolymers as prepared above.
  • Table 1 Example Comparative Example 1 2 3 4 1 2 Acrylic copolymer 100 100 100 100 100 100 100 100 Multi-function A 15 15 15 - - 15 Multi-function B - - - 20 20 - Hardner 1.0 1.0 1.0 1.0 1.0 1.0 LPO 2.5 - - - - - BPO - 2.5 - - - - THP - - 2.5 2.5 - - Irg500 - - - - 1.0 1.0 M812 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Multi-function A: hexafunctional acrylate Multi-function B: trifunctional acrylate(tris(meth)acryloxy ethyl isocyanurate) Hardner: XDI isocyanate(D110N) LPO: lauryl peroxide (10 hours half
  • the prepared pressure-sensitive adhesive layer was left in a constant temperature and humidity chamber (23°C, 60% RH) for about 7 days. Then, about 0.3 g of the pressure sensitive adhesive was poured into a stainless 200 mesh wire net and dipped into 100 ml of ethyl acetate. The resulting product was stored in a dark room at room temperature for 3 days. Then, the insoluble content was separated and dried in an oven at 70°C for 4 hours. Then, its weight was measured and the gel fraction was measured using it.
  • the prepared polarizer was cut in a size of 25 mm ⁇ 100 mm (width ⁇ length) to prepare a sample, and then adhered to an alkali-free glass using a laminator after removing the releasing sheet. Then, the resulting product was pressed in autoclave (50°C, 0.5 atmospheres) for about 20 minutes, and stored in the Temperature and Humidity Room Chamber (23°C, 50% RH) for 24 hours. Then, adhesion strength was measured under a condition in a detachment speed of 300 mm/min and a detachment angle of 180 degrees using Texture analyzer(Stable Micro Systems Ltd. (UK)), and evaluated re-movability through this measurement, based on the following basis.
  • the prepared polarizer was cut in a size of 180 mm ⁇ 250 mm (width ⁇ length) to prepare a sample, and said sample was attached to a 19 inch panel on market by using laminator. Then, the resulting product was pressed in autoclave (50°C, 0.5 atmospheres) for about 20 minutes, and stored in the Temperature and Humidity Room Chamber (23°C, 50% RH) for 24 hours. Then, to evaluate moisture-heat resistance of the prepared specimens, they were left at a temperature of 60°C and a relative humidity of 90% RH for 500 hours and then evaluated formation of bubbles or peeling.
  • the evaluation of light transmission uniformity was carried out using the same specimen as that used for evaluating the endurance reliability.
  • a polarizer with attached pressure-sensitive adhesive layer was attached to a 26 inch monitor (manufactured by AU Optronics (TW)), stored under constant temperature and humidity conditions for 1 day, left in an oven at 80°C for 500 hours, and evaluated about light transmission uniformity of four side conferences in the monitor square.
  • the evaluation of light transmission uniformity was carried out by calculating an increasing ratio of luminance relative to center part of the monitor after determining luminance value in upper and lower sides of the monitor, and right and left side of the monitor, at regular intervals relative to center part of the monitor by using spectroradiometer CS-2000 (KONICA MINOLTA(JP)). At this time, higher increasing ratio of luminance value is calculated, more light leakage is generated.
  • the pressure-sensitive adhesive was prepared by applying heat to a pressure-sensitive adhesive composition between releasing films (MRF-38, thickness: 38 micron, manufactured by Mitsubishi (JP)) (in case of Comparative Example, UV irradiation). Then pressure-sensitive adhesive layer having a thickness of about 25 ⁇ m was prepared by aging the prepared pressure-sensitive adhesive under constant temperature and humidity condition (23°C, 50% RH) for 7 days. Then the releasing film, on which pressure-sensitive adhesive layer was formed, was cut in a size of 6 cm ⁇ 6 cm, and then the pressure-sensitive adhesive was uniformly rolled to prepare a pressure-sensitive adhesive bar. The pressure-sensitive adhesive bar was securely adhered to upper and lower chucks by rubber gasket in Texture analyzer (Stable Micro Systems Ltd.

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Claims (15)

  1. Composition adhésive autocollante comportant des réseaux d'interpénétration dans un état polymérisé,
    dans laquelle la composition comprend un copolymère acrylique, un agent de réticulation multifonctionnel, un acrylate multifonctionnel et un initiateur thermique,
    et dans laquelle les réseaux d'interpénétration comprennent une structure de réticulation primaire formée par la réaction du copolymère acrylique et de l'agent de réticulation multifonctionnel et d'une structure de réticulation secondaire formée par la réaction de l'acrylate multifonctionnel et de l'initiateur thermique.
  2. Composition adhésive autocollante selon la revendication 1, dans laquelle le copolymère acrylique a un poids moléculaire moyen en poids de 1 000 000 ou plus.
  3. Composition adhésive autocollante selon la revendication 1,
    dans laquelle le copolymère acrylique comprend un monomère d'ester d'acide (méth)acrylique, et un monomère contenant un groupe fonctionnel pouvant être réticulé.
  4. Composition adhésive autocollante selon la revendication 3,
    dans laquelle le copolymère acrylique comprend en outre un monomère contenant un groupe oxyde d'alkylène.
  5. Composition adhésive autocollante selon la revendication 4,
    dans laquelle le monomère contenant un groupe oxyde d'alkylène est un adduit d'oxyde d'alkylène d'acide (méth)acrylique.
  6. Composition adhésive autocollante selon la revendication 1,
    dans laquelle l'acrylate multifonctionnel est un ou plusieurs groupes sélectionnés parmi le groupe constitué d'acrylate trifonctionnel, d'acrylate tétrafonctionnel, d'acrylate pentafonctionnel et d'acrylate hexafonctionnel.
  7. Composition adhésive autocollante selon la revendication 1,
    dans laquelle l'acrylate multifonctionnel comprend une structure cyclique dans son squelette.
  8. Composition adhésive autocollante selon la revendication 1,
    dans laquelle l'acrylate multifonctionnel est compris dans une quantité de 5 à 40 parties en poids, par rapport à 100 parties en poids du copolymère acrylique.
  9. Composition adhésive autocollante selon la revendication 1,
    dans laquelle l'initiateur thermique a une température de demi-vie de 10 heures de 40°C à 80°C.
  10. Composition adhésive autocollante selon la revendication 1,
    dans laquelle l'initiateur thermique est un ou plusieurs groupes sélectionnés parmi le groupe constitué du composé azoïque, du composé ester peroxyde, du composé peroxyde de dicarbonate et du peroxyde acyle.
  11. Composition adhésive autocollante selon la revendication 1,
    dans laquelle l'initiateur thermique est compris dans une quantité de 0,1 à 10 parties en poids, par rapport à 100 parties en poids du copolymère acrylique.
  12. Composition adhésive autocollante selon la revendication 1,
    dans laquelle l'agent de réticulation multifonctionnel est compris dans une quantité de 0,1 à 3 parties en poids, par rapport à 100 parties en poids du copolymère acrylique.
  13. Polariseur, comprenant :
    un film polarisant ou un dispositif de polarisation ; et une couche adhésive autocollante qui est formée sur un ou les deux côtés dudit film polarisant ou dudit dispositif de polarisation,
    et comprend un produit durci de la composition adhésive autocollante selon l'une quelconque de la revendication 1 à la revendication 12.
  14. Polariseur selon la revendication 13,
    dans lequel la teneur en gel telle que représentée par la formule générale I est de 80 % à 99 % Teneur en gel % = B / A x 100
    Figure imgb0005
    dans laquelle A représente le poids de l'adhésif autocollant, et B représente le poids sec de contenu insoluble après dépôt de l'adhésif dans l'acétate d'éthyle à température ambiante pendant 48 heures.
  15. Affichage à cristaux liquides comprenant un panneau à cristaux liquides dans lequel le polariseur selon la revendication 13 est lié à un ou aux deux côtés de la cellule à cristaux liquides.
EP09700483.2A 2008-01-11 2009-01-05 Composition adhésive, et plaque polarisante adhésive et dispositif d'affichage à cristaux liquides la comprenant Active EP2226371B1 (fr)

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CN101910344B (zh) 2013-01-30
EP2226371A4 (fr) 2011-12-14
WO2009088191A2 (fr) 2009-07-16
TW200948916A (en) 2009-12-01
KR20090077652A (ko) 2009-07-15
JP6354109B2 (ja) 2018-07-11
CN101910344A (zh) 2010-12-08
TWI406920B (zh) 2013-09-01
WO2009088191A3 (fr) 2009-09-24
JP2014055298A (ja) 2014-03-27
JP2011509332A (ja) 2011-03-24
EP2226371A2 (fr) 2010-09-08
US20110205469A1 (en) 2011-08-25
US9487681B2 (en) 2016-11-08
KR101023837B1 (ko) 2011-03-22

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